It's perhaps fitting that Tomas Kaberle is the one helping Tomas Plekanec find his way in Toronto.

Much like Plekanec, who will face a former team for the first time in his professional hockey life on Saturday night when the Canadiens come to town, Kaberle had to quickly confront a move from the only NHL organization he'd ever known in 2011. He was drafted by the Leafs in 1996, logged almost 900 regular season games over 12 seasons with the club, along with another 77 in the playoffs, before he was was dealt — not unexpectedly — to Boston at the trade deadline.

“It’s hard when you played somewhere for so long — him almost a thousand games,” Kaberle, now 40, said of Plekanec during a recent interview with The Athletic.

The two have met up for a dinner a few times since Plekanec was dealt from Montreal late last month, but they've only briefly discussed Kaberle's experience switching sides to a division rival...